Hydrochloric Acid → HCID 178498575, compound

HRID 1947190Notes

Reaction equation

HRID 1947190 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:36])[NH:15][NH:16][C:17](=O)[C:18]3[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[C:21]([O:27][CH2:28][O:29][CH3:30])=[CH:20][C:19]=3[O:31][CH2:32][O:33][CH3:34])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[OH-].[K+].Cl.C(=O)([O-])O.[Na+]>>[CH:24]([C:22]1[C:21]([O:27][CH2:28][O:29][CH3:30])=[CH:20][C:19]([O:31][CH2:32][O:33][CH3:34])=[C:18]([C:17]2[N:13]([C:10]3[CH:11]=[CH:12][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:8][CH:9]=3)[C:14]([OH:36])=[N:15][N:16]=2)[CH:23]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59829844HCID 59829844, compound

Product 1

HCID 178498575HCID 178498575, compoundYield 16.1%

Conditions

Temperature
105 °C

Procedure

4-[4-(morpholin-4-yl)-phenyl]-1-[5-isopropyl-2,4-bis(methoxymethoxy)-benzoyl]semicarbazide (IM5-O-a01: 104.9 mg, 0.209 mmol) was mixed with 5% aqueous sodium hydroxide solution (2 mL) and stirred 105° C. (bath temperature) for 2 hours. Further, potassium hydroxide (100 mg) was added to the reaction mixture and the resulting mixture was stirred at 130° C. (bath temperature) for 3 hours. After cooling to room temperature, the reaction mixture was neutralized with 2 N hydrochloric acid and aqueous sodium hydrogencarbonate, extracted with dichloromethane (50 mL) and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol=20:1) to obtain the title compound (IM6-O-a01: colorless syrup, 16.3 mg, 16%).

Workup

  1. stirringthe resulting mixture was stirred at 130° C. (bath temperature) for 3 hours
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with dichloromethane (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol=20:1)

Sources & evidence

ORD record
ord-6e80885526264fd28486b63d8f6086ee
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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